Oswego Homes under $500,000

Welcome to Oswego, Illinois: A Hidden Gem in Kendall County

Nestled along the scenic banks of the Fox River, Oswego is a charming village that beautifully balances small-town warmth with modern conveniences. Located in Kendall County, just a short drive from the bustling city of Chicago, Oswego offers residents a tranquil escape without sacrificing access to urban amenities. With its rich history, vibrant community spirit, and stunning natural surroundings, it’s no wonder that Oswego has become a sought-after destination for families and individuals alike.

Oswego boasts a delightful array of parks, recreational facilities, and scenic trails, making it an outdoor lover's paradise. The village hosts numerous community events throughout the year, fostering strong connections among residents. From farmers’ markets to summer festivals, there’s always something happening in this lively community.

When it comes to real estate, Oswego offers a diverse selection of homes under $500,000, making it an attractive option for first-time homebuyers and those looking to settle down in a welcoming environment. Whether you’re seeking a cozy single-family home with a spacious backyard, a modern townhouse with contemporary finishes, or a charming historic property, Oswego has something to suit every taste and budget.

With excellent schools, a variety of shopping and dining options, and easy access to major highways, Oswego is not just a place to live; it’s a place to thrive. Discover the beauty and charm of Oswego today, and find your dream home in this delightful community!

Newest Oswego Homes under $500,000

$275,000

3 Beds ⋅ 3 Baths ⋅ 12785015 MLS ⋅ NEW Status

Welcome home to this beautifully maintained 3-bedroom, 2.5-bathroom two-story condo! As an end unit, this home offers added privacy and peaceful views from your patio that backs up to a tree lined setting. The bright, inviting main level features durable laminate flooring and kitchen with stainless steel appliances. Upstairs, you'll find three comfortable bedrooms, including a spacious primary suite with walk in closet. Enjoy the ease of an attached garage and the low-maintenance lifestyle condo living provides. With a desirable layout, great natural views, and plenty of space to call your own, this home is a must-see! Many updated done including: new Carpet 2024, New washer and dryer 2025, new dishwasher 2025, new garage door opener 2024, new nest theromstat 2026, garbage disposal 2021, and roof in 2018.

109 Waterbury Circle Unit #109, Oswego

$389,900

3 Beds ⋅ 4 Baths ⋅ 12782679 MLS ⋅ NEW Status

East-Facing Former Builder's Model Home with Beautiful Water Views and 2,861 Sq. Ft. of Living Space. Why settle for less space when you can have it all? At 199 Dorset Avenue, you'll find more room than many single-family homes, including three spacious bedrooms, two full and two half bathrooms, a finished lower level, and a two-car attached garage-all with the convenience of low-maintenance living. Step inside to a bright, welcoming main level featuring elegant wainscoting, hardwood flooring, and a warm gas fireplace. The oversized kitchen is perfect for everyday living and entertaining, with Merillat cabinetry, granite countertops, stainless-steel appliances, a center island, breakfast bar, pantry, and plenty of workspace. The open layout connects naturally with the dining and living areas. Upstairs, the primary suite provides a comfortable private retreat with two custom-organized walk-in closets and a spa-inspired bathroom featuring dual sinks, a jetted tub, and a separate full-body spray shower. Two additional bedrooms, another full bathroom, and convenient second-floor laundry complete the upper level. Need additional space? The finished lower level offers outstanding flexibility, with a large recreation or media room, space for a home office, gym or game area, another half bathroom and ample storage. Outside, begin your mornings or relax in the evenings on the private patio overlooking the water. Prairie Point Community Park is only steps away, keeping trails, recreation, and green space within easy reach. At only $195 per month, the association includes exterior maintenance, lawn care, snow removal, and insurance. You will also enjoy access to the community clubhouse, swimming pool, and fitness center. Located in Oswego School District 308, 199 Dorset Avenue offers a rare combination of spacious living, peaceful surroundings, desirable amenities, and low-maintenance convenience. Schedule your private showing and experience it for yourself.

199 Dorset Avenue, Oswego

$425,000

4 Beds ⋅ 3 Baths ⋅ 12784159 MLS ⋅ NEW Status

Discover the potential in this spacious 4-bedroom, 2.5-bath home in the heart of Oswego, offering generous living spaces, a functional floor plan, and several major recent updates. A welcoming two-story foyer sets the tone as you enter, while large windows throughout fill the home with an abundance of natural light. The thoughtfully designed layout provides plenty of space for everyday living, entertaining, and working from home. Fresh interior paint and brand-new carpeting create a clean, neutral foundation, while still offering the next owner the opportunity to add their own style and personal touches. The partially finished basement adds valuable additional living space and features a dry bar-perfect for a recreation room, home office, fitness area, playroom, or game-day gatherings. Step outside to a generously sized backyard offering endless possibilities for outdoor entertaining, gardening, play, or simply relaxing and enjoying the outdoors. Major recent improvements add even more value, including a brand-new roof (August 2026), new water heater (July 2026), new air conditioner, and whole-home interior paint (Spring 2026), plus new carpet (summer 2026). Conveniently located near parks, walking trails, shopping, dining, and Oswego-area schools, this home offers the ideal combination of space, location, recent improvements, and opportunity. This home is ready for immediate occupancy plus has instant sweat equity to be made! Make it your own. Some photos are virtually staged to give you ideas of what you can do with the space.

418 Terrace Lane, Oswego

$350,000

4 Beds ⋅ 3 Baths ⋅ 12776567 MLS ⋅ NEW Status

Welcome home to a space that offers more than you might expect, with three levels of flexible living and thoughtful updates throughout. Located in Oswego's sought after Southbury community, this 4 bedroom, 2.1 bath townhome offers comfort, convenience, and versatility for everyday living. Step inside and head upstairs to the heart of the home, where hardwood floors connect the spacious living and dining areas to a kitchen designed for both everyday living and entertaining. Featuring a large island, ample cabinetry, table space, and access to the deck, this inviting space makes it easy to gather and unwind. Upstairs, three comfortable bedrooms offer a private retreat from the main living areas. The primary suite features its own full bathroom and walk in closet, while conveniently located laundry adds ease to everyday routines. The finished walkout lower level provides even more possibilities, featuring a fourth bedroom currently used as a home office, with fresh carpeting installed in 2026, a spacious closet, and sliding glass doors leading directly to the patio. Whether used as a guest bedroom, home office, workout room, or additional living space, this versatile room offers flexibility to suit a variety of needs. The lower level also provides convenient access to the attached 2 car garage. Several important updates have already been completed, including a new furnace and A/C in 2022, whole house water filtration and an additional under sink kitchen filtration system, an updated dishwasher, gas range, kitchen sink and faucet, and stackable washer and dryer. Beyond the home, Southbury offers community amenities including pools, a clubhouse, fitness center, parks, and playgrounds. With thoughtful updates, flexible living spaces, and community amenities to enjoy, this townhome offers a wonderful opportunity to settle in, make it your own, and enjoy everything Southbury has to offer.

142 Lakeshore Drive, Oswego

$345,000

2 Beds ⋅ 3 Baths ⋅ 12783632 MLS ⋅ NEW Status ⋅ Churchill Club BLDG.

This beautifully updated end-unit townhome is now available in the highly desirable Churchill of Oswego! The home has been completely refreshed in today's trendy colors and finishes, making it a distinctive choice. Boasting the largest 2-bedroom floorplan at nearly 2,000 sq. ft. - comparable to the larger 3-bedroom models - it offers potential options for conversion if desired. Upon arrival, the inviting covered front porch greets you. Inside, you will find an impressive two-story Entry and Living Room filled with natural light, sure to leave a lasting impression. The Kitchen has been exquisitely updated with high-end stainless appliances, 42-inch cabinets, and elegant quartz countertops and island, seamlessly connecting to the cozy Family Room. A separate Dining Room (or flex room) is conveniently situated off the Kitchen, along with a Laundry Room equipped with front-load washer and dryer on pedestals and a refreshed Powder Room, making the first floor highly functional. Upstairs, the spacious Primary Suite features 3 closets and a beautifully updated Bathroom with a quartz countertop and a luxurious floor-to-ceiling shower enclosure complete with built-ins and a high-end shower head. The 2nd Bedroom and nicely updated Hall Bathroom are thoughtfully positioned on the opposite side of the home. A spacious and versatile Loft awaits, adaptable to your needs. The finished 2-Car Garage includes overhead storage mounted to ceiling. Enjoy the picturesque sunsets from the privacy of your patio and backyard. This home has been lovingly maintained by the current owner along with 2 former owners. RECENT UPDATES INCLUDE: total Kitchen redo, vinyl plank flooring throughout, white doors & trim and hardware, A/C, HWH, water softener, Primary Bathroom, and 2nd Bathroom. Living in Churchill Club, you'll enjoy fantastic resort-style amenities, including a clubhouse, outdoor pool with waterslide, splash pad, exercise room, gathering rooms, tennis/pickleball courts, sand volleyball court, playgrounds, parks, walking trails, and so much more. The highly regarded District 308 schools - including Churchill Elementary, Plank Junior High, and the Brokaw Early Learning Center - are all within the community, with Oswego East High School just a short distance away. Plus, shopping, dining, entertainment and daily conveniences are nearby. Offering modern updates, a premium location, top-tier amenities, and move-in-ready condition, this exceptional home presents a rare opportunity in one of Oswego's most sought-after communities!

483 Dancer Lane, Oswego

$419,990

3 Beds ⋅ 3 Baths ⋅ 12783148 MLS ⋅ NEW Status

Welcome to 2437 Semillon St. the Bradley floorplan at the beautiful amenity filled Sonoma Trails Community in Oswego, IL. This home is ready for a quick move-in! Step inside this 1,663 square foot home with 3 bedrooms, 2.5 baths, a loft, 2-car garage and smart home technology. Entering the foyer, you will first pass the powder room, and then walk into the main level living space. The living area is open concept, with your bump out dining area, a living room, and kitchen blend together seamlessly. The kitchen shows off beautiful designer 42" cabinetry, a pantry, and an island with ample seating space that looks out to the living room. This layout is great for entertaining family and friends. Heading up the beautiful rod iron staircase you'll find a loft which is perfect as a home office or study space! Your primary bedroom features a deluxe bath with ample storage in the walk-in closet, and a dual sink vanity. 2 additional bedrooms with closets, a second bath, linen closet, and a convenient upstairs laundry room complete the rest of the second floor. All Chicago homes include our America's Smart Home Technology. Exterior/interior photos of similar home, actual home as built may vary.

2437 Semillon Street, Oswego

$330,000

2 Beds ⋅ 1 Baths ⋅ 12782732 MLS ⋅ NEW Status

Discover a rare Fox Riverfront home for sale in Oswego, Illinois! Situated on a 1.05-acre lot directly across from the Fox River and Veterans Serenity Park, this property offers stunning year-round water views and immediate access to the Fox River Trail right outside your front door. Perfect for biking, jogging, or scenic walks, this location combines outdoor recreation with small-town charm. This 2-bedroom, 1-bath home offers 1,200 sq. ft. of living space filled with natural light. The inviting living room features warm wood-accent walls, a bay window overlooking the park and river, and an open layout that flows into the dining space-ideal for entertaining. The bright kitchen has vaulted ceilings, tile flooring, and plenty of potential for customization. A full basement provides additional storage or expansion space. Car lovers, mechanics, and hobbyists will appreciate the oversized 3-car garage with an extra-high overhead door, perfect for storing boats, RVs, and other outdoor toys. A storage shed is also included. The spacious deck is ideal for morning coffee, weekend BBQs, and watching the sunset over the water. Located just minutes from downtown Oswego's shops, restaurants, and community events, this property offers both tranquility and convenience. Whether you're seeking a single-family home with river views, a vacation home in Oswego, or a prime redevelopment lot in Kendall County, 34 N Adams St is a one-of-a-kind opportunity.

34 N Adams Street, Oswego

354 Ogden Falls Boulevard Unit #354, Oswego

$219,000

2 Beds ⋅ 1 Baths ⋅ 12782156 MLS ⋅ ACTIVE Status ⋅ Ogden Falls BLDG.

Welcome to 354 Ogden Falls Blvd in Oswego! This well-maintained 2-bedroom home features a bright, open-concept layout with hardwood floors throughout the main living areas. The spacious living room is centered around a beautiful stone fireplace and flows seamlessly into the dining area and kitchen. The kitchen offers ample cabinetry, stainless steel appliances, and plenty of counter space. Both bedrooms offer great natural light and closet space, with additional conveniences including in-unit laundry and an attached garage. Step outside to your private deck, perfect for relaxing or entertaining. Conveniently located near shopping, dining, parks, and everything Oswego has to offer. Move-in ready and ready to welcome you home!

354 Ogden Falls Boulevard Unit #354, Oswego

$482,250

3 Beds ⋅ 3 Baths ⋅ 12780227 MLS ⋅ ACTIVE Status

FIRST-FLOOR MASTER! READY TO CLOSE. Welcome to Harvest Gate at Southbury- our most affordable premier master planned community in Oswego! This exciting new single-family community includes full unfinished basements. Imagine the ease of walking your kids to Southbury Elementary and Traughber Junior High, then spending weekends enjoying a resort-style 7600 sq ft clubhouse with two sparkling pools, tennis, pickleball, and volleyball courts, walking and biking trails, playground, and picnic areas. This gorgeous new Harrison comes with a first-floor primary bedroom suite including a full bath. Your foyer leads to the soaring two-story great room, with the dining area and kitchen in the back overlooking the patio...a great gathering place for family and friends. Your chef-inspired kitchen has built-in SS Whirlpool appliances - oven, cooktop, vented hood - pristine Frost cabinets with granite counters, and a ceramic tile backsplash. You have a large island with room for seating and pendant lights. Your first-floor primary bedroom suite is tucked away for your complete privacy and includes a luxury bath with large shower and a comfort-height double bowl vanity. The 2nd floor loft is perfect for games or family movie nights. Two additional bedrooms and a family bath complete the 2nd floor. Additional upgrades include Smart Home package including garage door opener. Designer details feature wrought iron rail and spindle stairs, brushed nickel finishes and 7" wide vinyl wood plank flooring the entire first floor. Photos of this beautiful home! READY TO CLOSE!

141 Daltrey Drive, Oswego

$429,900

4 Beds ⋅ 3 Baths ⋅ 12781384 MLS ⋅ ACTIVE Status

Immediate Occupancy!! Freshly painted throughout!! This beautiful 4 bedroom, 2.5 bath home offers spacious living areas, wood and tile flooring and exceptional features both inside and out! Soaring 2 story entry with 16" ceramic tiles through to the kitchen. Hardwood flooring in living room,dining room and family room.The spacious kitchen features abundant cabintry, buffet area and large pantry. A charming butler's pantry connect the kitchen to the formal dining room, creating the perfect setup for entertaining. Just off the kitchen, the inviting family room features a stunning stone fireplace, make it an ideal space to relax and unwind.The spacious primary suite offer a private bathroom with double sinks, a luurious whirlpool tub, and a separate shower. Three additional generously sized bedrooms and a full hall bathroom provide plenty of room for the family, guest or a home office. Additional highlights include a basement offering extra storage or potential for additional living space, and is plumbed for an additional bath. The professional landscaped yard and beautiful brick patio with a pergola is perfect for outdoor dining, entertaining, or simply enjoying the outdoors. Don't miss the opportunitey to make this beautiful home yours! Move in today and enjoy the space, charm and features this home has to offer.

207 Willington Way, Oswego

$399,000

4 Beds ⋅ 2 Baths ⋅ 12781314 MLS ⋅ ACTIVE Status

Beautifully updated and ideally located just minutes from downtown Oswego, this home puts parks, shopping, and restaurants within walking distance! Renovated approximately five years ago, the bright kitchen showcases white soft close cabinetry, quartz countertops, new stainless steel appliances, and updated lighting. Its open layout connects the eat-in area and living room, creating an inviting space for everyday living and entertaining. New engineered hardwood flooring throughout adds warmth and a cohesive look, while the renovated bathrooms offer updated vanities and fresh paint. The entire exterior has also been repainted, giving the home a fresh, welcoming look and added curb appeal. Major mechanicals, including the roof and windows, have all been replaced within the past 10-12 years, providing added peace of mind. Enjoy extensive updates and convenient access to everything Oswego has to offer!

147 Monroe Street, Oswego

$485,000

4 Beds ⋅ 4 Baths ⋅ 12735493 MLS ⋅ ACTIVE Status

If you've been dreaming of summers by the pool, parks just down the street, and weekend strolls into downtown Oswego, this home has it all. Four bedrooms, three full baths plus a powder room, and a backyard built for living outside. The oversized Trex deck has room for it all: a sunny spot for lounging, a seating area for relaxing, and a dining space with the grill close by, all overlooking the above-ground pool. Because it's Trex, you spend your weekends enjoying the deck and pool instead of working! Main floor is spacious with an office, family room, living room and formal dining room. The kitchen has stainless steel appliances, and first-floor laundry makes everyday chores easier. The finished basement adds even more living space... you can use as a rec room, media room, home gym, or guest area. A three-car garage has room for the cars plus the bikes, pool floats, and everything else. Prairie View Park and Lakeview Park are both close by, downtown Oswego and its farmers market are within walking distance, and the home is served by District 308 schools, including Prairie Point Elementary and Oswego High School.

502 Saratoga Court, Oswego

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